Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
  • C07D213/40—Acylated substituent nitrogen atom
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P25/00—Drugs for disorders of the nervous system
  • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C317/00—Sulfones; Sulfoxides
  • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
  • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
  • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
  • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
  • C07D213/52—Sulfur atoms

Definitions

• the present invention relates to acetamide derivatives which can be used therapeutically as modifiers of food intake behavior.
• the present invention aims to provide new acetamide derivatives which are characterized by a modifying or regulating effect on food intake behavior in humans and animals.
• R ⁇ is chosen from H and 3-chloro
• R 2 is chosen from a phenyl group and a pyridyl group
• R 3 and R 4 are chosen independently of one another from H and methyl
• R lt R 3 , R 4 , R 5 and R 6 not being simultaneously H when R 2
• the compounds of formula I can be obtained according to known methods.
• the thioacetamides of formula II can be obtained in particular by reaction of a reactive derivative of an acid of formula:
• Z is a reactive group, in particular Cl or
• the compounds according to the invention can be used in therapy as modifiers or regulators of the behavior of food intake in humans and animals.
• the present invention therefore also relates to therapeutic compositions comprising an effective amount of a compound of formula I or of the salts of the compounds of formula with a pyridine group with pharmaceutically acceptable acids.
• 1'invention can be administered including oral.
• They can be in the form of solid or semi-solid preparations.
• compositions make it possible in particular to delay food intake and can therefore constitute a precious aid for regulating weight, in particular in individuals who are following a diet.
• Effects on grip behavior food have been demonstrated using a test in mice according to a method described by Ladurelle et al. (Funda. Clin. Pharmacol., 5, 481).
• the product is a white powder, insoluble in ether, ethyl acetate, slightly soluble in alcohols. Its solubility in water is less than 0.1%.
• a solution of 10.2 g (0.13 mole) of thiourea in 100 ml of water is heated to 40 ° C., 28.8 g (0.12 mole) of the hydrochloride obtained in a) are added and the mixture is heated for 10 minutes. reflux.
• a solution of 24 g (0.6 mole) of sodium hydroxide in 150 ml of water is added at 50 ° C. and the mixture is heated for 10 minutes at reflux.
• the methyl ester is dissolved in 100 ml of methanol and 50 ml of 28% ammonia are added, after 48 hours in contact, evaporated to dryness under vacuum, taken up with 100 ml of water, drained and dried.
• the product is a white powder, insoluble in ether, very slightly soluble in ethyl acetate, acetone, alcohols. Its solubility in water is less than 0.1%.
• the product is a white powder, insoluble in ether, slightly soluble in ethyl acetate, soluble in alcohols. Its solubility in water is around 0.1%.
• the precipitate obtained is filtered, the methylene chloride is evaporated, taken up in ether, washed with water, extracted with a dilute HCl solution, filtered the insoluble material, precipitated with a concentrated NaOH solution and wring.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Pharmacology & Pharmacy (AREA)
• Biomedical Technology (AREA)
• Neurology (AREA)
• Neurosurgery (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Pyridine Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Fats And Perfumes (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Priority Applications (7)

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Citations (3)

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• 1993
  • 1993-06-30 FR FR9308008A patent/FR2707637B1/fr not_active Expired - Fee Related
• 1994
  • 1994-06-30 EP EP94921005A patent/EP0706512B1/fr not_active Expired - Lifetime
  • 1994-06-30 CA CA002166128A patent/CA2166128A1/fr not_active Abandoned
  • 1994-06-30 AU AU71890/94A patent/AU677852B2/en not_active Expired
  • 1994-06-30 DE DE69409525T patent/DE69409525T2/de not_active Expired - Lifetime
  • 1994-06-30 KR KR1019950705999A patent/KR100332154B1/ko not_active IP Right Cessation
  • 1994-06-30 AT AT94921005T patent/ATE164837T1/de active
  • 1994-06-30 ES ES94921005T patent/ES2117795T3/es not_active Expired - Lifetime
  • 1994-06-30 JP JP7503323A patent/JPH11500406A/ja active Pending
  • 1994-06-30 NZ NZ268614A patent/NZ268614A/en not_active IP Right Cessation
  • 1994-06-30 US US08/564,284 patent/US5719168A/en not_active Expired - Lifetime
  • 1994-06-30 WO PCT/FR1994/000803 patent/WO1995001333A1/fr active IP Right Grant

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